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Why Do We Crossdress?

Why do We Crossdress

"...the journey of crossdressing is like climbing a hill and finding, upon reaching the top, another, higher hill waiting in the distance. We are always driven forward by the promise and the mystery of what lies on the other side."

Over the years, I have avoided for the most part asking this question of others or trying to answer it for myself. The reason I steered clear of this one is that trying to answer it can get in the way of something more important: learning to accept the fact that we crossdress. I don't want to feel that unless I can explain why, I am not free to enjoy it.

Before I get too far into this discussion, I’d like to clarify what I mean by the word “crossdress”.

When I did my on-line survey in 1999, I discovered that only about half the people who said they crossdressed were actually going to the point of applying makeup, putting on a wig (or styling their own hair to be more feminine) and in general present themselves as a woman or trying to “pass”.

The other half crossdress from the neck down.

I am not being judgmental or critical of anyone, and I certainly won’t claim that one approach to crossdressing is better than any other. Everyone lives with their own sense of what they are comfortable with and what they can handle.

The reason I mention this is that I sometimes hear crossdressers describe themselves as “typical, normal men”… who happen to like to make themselves look like women. Forgetting for a moment the use of loaded words like “normal”, I have to admit to exasperation with this one. It is, to me, either denial or a vain attempt at having it both ways. Crossdressers are anything but typical men. We may live ordinary lives, but we live them in an extraordinary way.

What I do know is this: living almost all of one’s life with crossdressing is an ongoing process of moving between fantasy and reality.

The fantasy is what we think we are capable of, what we think we can become, who we think we can be. These fantasies become reality by taking small steps, living now while dreaming about the future. When we are young, many of us fantasized about being turned into women, through some technology or magic, or being given the power to transform ourselves back and forth between male and female at will.

When I was a small child, totally dependent on my parents and with no control over my own life, I often wondered what it would feel like to be a girl: to wear my long hair in a pony tail or to have it braided, to wear dresses and skirts and Mary Jane shoes, to have to walk and sit and bend down differently.

When I got a little older, I was able to obtain some articles of women’s clothing of my own and try them on. I discovered what it felt like to dress differently, and in the process what had been only fantasy became reality. As time went on, I experimented with more clothing, wigs and makeup and began to develop an image of myself as female, at least in appearance if nothing else.

This was becoming my reality.

But the journey of crossdressing is like climbing a hill and finding, upon reaching the top, another, higher hill waiting in the distance. We are always driven forward by the promise and the mystery of what lies on the other side.

We all face many of the same hills, some are harder to climb than others.

I remember once, as a teenager, shaving my legs during the summer to just above the knees. It was both terrifying and exciting because of what I was both losing and gaining.

I remember another time, going out late at night crossdressed and just walking around the block in my neighborhood, again terrified of being caught or even seen by someone, but thrilled by the sensation and the achievement.

Sometimes the terror became too great, and out of fear I would turn around on my path, and decide I didn’t want to climb any more hills. I sometimes felt like I was killing off my male self for the sake of some as of yet unknown female self. In these times, I would nurture my masculine self.

We call these moments “purges” and, as we all know, they are only temporary. In time, we start on our path again.

I was lucky. I never resorted to risky, self-destructive behavior in an effort to destroy the female in me (by killing off the male host). I never joined the military, never drank excessively, never used the trappings of machismo to hurt or punish myself.

But the journeys of many crossdressers are filled with stories like that.

For me it was different. I resorted to sabotage in an effort to destroy my host. Rather than kill the body, I tried to kill the mind. How did I do that? By marrying a woman who knew I was a crossdresser and who hated it. I punished myself with thirteen years of a loveless relationship with someone who was repulsed by the person I fundamentally was.

And to make sure I suffered, I kept my body alive and well. On the outside, one might have even thought I was flourishing. Little did they, or I, know or understand that I had, of my own choice and free will, locked myself away in a jail cell from which I could see in the far distance, through a tiny window, the hills I would never allow myself to climb.

But that period of my life is over, and I don’t dwell on it. I recall a line from a popular song I heard when I was a teenager:

“Don’t let the past remind us of what we are not now”

There were hills to climb and I had wasted too much time already.

But what starts us on this path with these hills? When we are very young, and we are faced with our first hill, what compels us or motivates us to climb?

Is it something in our bodies, some chemical that makes it seem right to do so? Is it our nature? Or is it the fact that there was no internal voice telling us not to, no message that says this is not our path? Is it the way we were nurtured?

Personally, I think it has more to do with how we are brought up than something organic within our bodies. Children are born perfect, with no sense of evil, no fear, no notion of what is expected of them. Children are guiltless, innocent, free. It would only make sense that the longer a child remains so, the more likely he or she is to experiment with that same sense of innocence and wonder.

The shame and guilt comes later.

Perhaps there is some biological explanation as well and it is a combination of biological and environmental factors. How else can you explain the fact that no one ever chooses to stop, and if they do, it’s not for long.

Or perhaps there is no one single explaination for why we do what we do. Perhaps that's the myopic shortcoming of science: to try to keep everything else equal and explain human behavior with respect to a single random variable. Perhaps the very act of answering this question causes the answer itself to change.

There is, at any rate, something very compelling about crossdressing, something that makes us want to climb those hills and see what’s on the other side. Our reasons for crossdressing change with time, we climb new and different hills. I am no longer an eight year old child wondering. I've climbed that hill and many others.

If you want to understand why you crossdress, consider the hill you are climbing and what you expect to find at the top.

And yes, I am aware that I haven’t answered the question.

Written by Yvonne, a married crossdresser with a supportive partner that lives in the Albany, New York area. Visit her site at:

Do you have a story you'd like to share about your experiences with crossdressing? Please send to and we will consider adding your story to our site.


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